Synthesis and Stereochemical Assignment of (+)-chamuvarinin

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2010 Dec 23

PMID 21174397

Citations 5

Authors

Gordon J Florence

Joanne C Morris

Ross G Murray

Jonathan D Osler

Vanga R Reddy

Terry K Smith

Affiliations

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Abstract

A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15-C28 ether array, followed by a late-stage Julia-Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin.

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